Click synthesis and biologic evaluation of (R)-and (S)-2-Amino-3-[1-(2- [18F]Fluoroethyl)-1H-[1,2,3]Triazol-4-yl]propanoic acid for brain tumor imaging with positron emission tomography

Molecular Imaging

Volumn 9, Issue 6, 2010, Pages 329-342

  McConathy, Jonathan ^a,b,c   Zhou, Dong ^a,b,c   Shockley, Stephany E ^a,b,c   Jones, Lynne A ^a,b,c   Griffin, Elizabeth A ^a,b,c   Lee, Hsiaoju ^a,b,c   Adams, Susan J ^a,b,c   Mach, Robert H ^a,b,c  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c Molecular Neuroimaging   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

9L GLIOSARCOMA; BACKGROUND RATIO; BIODISTRIBUTIONS; BRAIN TUMOR IMAGING; BRAIN TUMOR MODEL; BRAIN TUMORS; CATIONIC AMINO ACIDS; CELL UPTAKE; CLICK REACTION; IN-VITRO; IN-VIVO; MICROPET; PROPANOIC ACID; TIME POINTS; TUMOR IMAGING; TUMOR UPTAKE;

AMINO ACIDS; CHIRALITY; ENANTIOMERS; POSITRONS; SYNTHESIS (CHEMICAL); TUMORS;

POSITRON EMISSION TOMOGRAPHY;

2 AMINO 3 (1 (2 FLUOROETHYL) 1H (1,2,3)TRIAZOL 4 YL)PROPANOIC ACID; 2-AMINO-3-(1-(2-FLUOROETHYL)-1H-(1,2,3)TRIAZOL-4-YL)PROPANOIC ACID; ALANINE; DIAGNOSTIC AGENT; DRUG DERIVATIVE; PROPIONIC ACID DERIVATIVE; TRIAZOLE DERIVATIVE;

ANIMAL; ARTICLE; BLOOD; BRAIN TUMOR; CHEMISTRY; CLICK CHEMISTRY; FISCHER 344 RAT; GLIOSARCOMA; HUMAN; METABOLISM; METHODOLOGY; PATHOLOGY; POSITRON EMISSION TOMOGRAPHY; RAT; SCINTISCANNING; SUBCUTANEOUS TISSUE; SYNTHESIS; TIME; TISSUE DISTRIBUTION;

ALANINE; ANIMALS; BRAIN NEOPLASMS; CLICK CHEMISTRY; GLIOSARCOMA; HUMANS; POSITRON-EMISSION TOMOGRAPHY; PROPIONATES; RATS; RATS, INBRED F344; SUBCUTANEOUS TISSUE; TIME FACTORS; TISSUE DISTRIBUTION; TRIAZOLES;

EID: 78649758969     PISSN: 15353508     EISSN: None     Source Type: Journal    
DOI: 10.2310/7290.2010.00025     Document Type: Article

References (38)

1. 11C]-L-Methionine positron emission tomography in the clinical management of cerebral gliomas. Mol Imaging Biol 2008;10:1-18.
2. 18F] Fluoroethyl)-L-tyrosine: uptake mechanisms and clinical applications. Nucl Med Biol 2006;33:287-94.
3. 18F-FDG PET and evaluation of diagnostic accuracy. J Nucl Med 2006;47:904-11.
4. 123I]Iodo-alpha-methyl- Ltyrosine: uptake mechanisms and clinical applications. Nucl Med Biol 2002;29:625-31.
5. McConathy J, Goodman MM. Non-natural amino acids for tumor imaging using positron emission tomography and single photon emission computed tomography. Cancer Metastasis Rev 2008;27: 555-73.
6. 18F Alpha-methyl tyrosine PET studies in patients with brain tumors. J Nucl Med 1999;40: 399-405.
7. 18F-FDOPA PET. J Nucl Med 2004; 45:1161-7.
8. Montravers F, Grahek D, Kerrou K, et al. Can fluorodihydroxyphenylalanine PET replace somatostatin receptor scintigraphy in patients with digestive endocrine tumors? J Nucl Med 2006;47: 1455-62.
9. 18F-fluorocyclobutane-1-carboxylic acid with PET/CT in prostate carcinoma. J Nucl Med 2007;48:56-63.
10. 18F-fluorocyclobutyl-1-carboxylic acid for the detection of prostate cancer. J Nucl Med 2007;48:46-55.
11. Fuchs BC, Finger RE, Onan MC, et al. ASCT2 silencing regulates mammalian target-of-rapamycin growth and survival signaling in human hepatoma cells. Am J Physiol Cell Physiol 2007;293:C55-63.
12. Fuchs BC, Bode BP. Amino acid transporters ASCT2 and LAT1 in cancer: partners in crime? Semin Cancer Biol 2005;15:254-66.
13. Esseghir S, Reis-Filho JS, Kennedy A, et al. Identification of transmembrane proteins as potential prognostic markers and therapeutic targets in breast cancer by a screen for signal sequence encoding transcripts. J Pathol 2006;210:420-30.
14. Nawashiro H, Otani N, Shinomiya N, et al. L-type amino acid transporter 1 as a potential molecular target in human astrocytic tumors. Int J Cancer 2006;119:484-92.
15. Demko ZP, Sharpless KB. An intramolecular [2 + 3] cycloaddition route to fused 5-heterosubstituted tetrazoles. Org Lett 2001;3:4091-4.
16. Mindt TL, Struthers H, Brans L, et al. ''Click to chelate'': synthesis and installation of metal chelates into biomolecules in a single step. J Am Chem Soc 2006;128:15096-7.
17. 18F] fluoroethylazide for positron emission tomography. Bioconjug Chem 2007;18:989-93.
18. 18F]fluoromethyl-cyclobutane-1-carboxylic acid (FMACBC), potential PET ligands for tumor detection. J Med Chem 2002;45:2250-9.
19. 18F]fluoro-2-methyl-2-(methylamino)propanoic acid. J Med Chem 2002;45:2240-9.
20. 18F]fluoro-2-methylbutanoic acid (FAMB): relationship of amino acid transport to tumor imaging properties of branched fluorinated amino acids. Nucl Med Biol 2003;30:477-90.
21. 18F]1-amino-3-fluorocyclobutane-1-carboxylic acid to image brain tumors. J Nucl Med 1999;40:331-8.
22. 123I]iodo- 3-(E)-butenoic acid for brain tumor imaging with single photon emission computerized tomography. J Med Chem 2007;50: 6718-21.
23. 18F]fluoroethyl)-D-tyrosine (D-FET) into the porcine brain. Brain Res 2007;1147:25-33.
24. 18F]fluoro-proline at the bloodbrain barrier. J Cereb Blood Flow Metab 2005;25:607-16.
25. Gazzola GC, Dall'Asta V, Franchi-Gazzola R, et al. The cluster-tray method for rapid measurement of solute fluxes in adherent cultured cells. Anal Biochem 1981;115:368-74.
26. La Regina MC, Culbreth VO, Higashikubo R, et al. An alternative method to stereotactic inoculation of transplantable brain tumours in large numbers of rats. Lab Anim 2000;34:265-71.
27. Shotwell MA, Kilberg MSOxender DL. The regulation of neutral amino acid transport in mammalian cells. Biochim Biophys Acta 1983;737:267-84.
28. Christensen HN, Oxender DL, Liang M, et al. The use of Nmethylation to direct route of mediated transport of amino acids. J Biol Chem 1965;240:3609-16.
29. Palacin M, Estevez R, Bertran J, et al. Molecular biology of mammalian plasma membrane amino acid transporters. Physiol Rev 1998;78:969-1054.
30. Closs EI, Boissel JP, Habermeier A, et al. Structure and function of cationic amino acid transporters (CATs). J Membr Biol 2006;213: 67-77.
31. Closs EI. Expression, regulation and function of carrier proteins for cationic amino acids. Curr Opin Nephrol Hypertens 2002;11:99-107.
32. Jager PL, Vaalburg W, Pruim J, et al. Radiolabeled amino acids: basic aspects and clinical applications in oncology. J Nucl Med 2001;42:432-45.
33. Wheatley DN. Arginine deprivation and metabolomics: important aspects of intermediary metabolism in relation to the differential sensitivity of normal and tumour cells. Semin Cancer Biol 2005;15: 247-53.
34. Wu G, Bazer FW, Davis TA, et al. Arginine metabolism and nutrition in growth, health and disease. Amino Acids 2009;37: 153-68.
35. 18F-FLT for differentiation between tumor and inflammation in rats. Nucl Med Biol 2009;36:681-6.
36. Moon BS, Lee TS, Lee KC, et al. Syntheses of F-18 labeled fluoroalkyltyrosine derivatives and their biological evaluation in rat bearing 9L tumor. Bioorg Med Chem Lett 2007;17:200-4.
37. Carvlin MJ, Rajan SS, Rosa L, et al. Efficacy of nonionic lowosmolar gadodiamide injection in animals with intracranial mass lesions. J Magn Reson Imaging 1992;2:19-24.
38. Wilkins DE, Raaphorst GP, Saunders JK, et al. Correlation between Gd-enhanced MR imaging and histopathology in treated and untreated 9L rat brain tumors.Magn Reson Imaging 1995;13:89-96.